#3 Khabib vs. Conor McGregor

Of course, if the UFC and Khabib decided on a fight that would draw more money than any other fight, there’s only one opponent that would make sense. Despite his one-sided loss to the Dagestani at UFC 229 in 2018, Conor McGregor remains the UFC’s most bankable star – as he proved in January when he drew a million pay-per-view buys alongside Donald Cerrone at UFC 246.
Would Khabib really be interested in facing McGregor again? Well, The Eagle has actually suggested he’s not. It was even reported that a figure of $100m wouldn’t be enough to tempt him to fight the Irishman in a rematch.
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However, the bad blood between the two still clearly exists, with Khabib labeling McGregor “an idiot” in the report mentioned above. The Notorious One is still sniping at the Dagestani on Twitter every now and then. And of course, everyone remembers the chaos that ensued after the fight at UFC 229.
With that in mind, it’d clearly be straightforward for the UFC to market a rematch. McGregor is a good enough talker to suggest that he’d be in with a chance – he could simply claim he’s improved or that he took Khabib lightly in the first bout. Whether that’s true or not is neither here nor there. McGregor’s fans would buy it, and that’s what would matter.
Interestingly, one man who seems to support the idea of a Khabib/McGregor rematch is Javier Mendez, one of the Dagestani’s coaches. Reportedly, Mendez believes the money that could be generated by the fight would simply be too good for Khabib to turn down.
Add in the fact that judging by the first fight, Khabib would be heavily favored, and suddenly, taking the fight makes more sense. If Khabib really wants to end his career at 30-0, then a McGregor rematch would definitely give him the best opportunity of doing so while also making an insane amount of cash at the same time.
#4 Khabib vs. Kamaru Usman

Some UFC fans might’ve had their fill of inter-divisional ‘Superfights’ over the past couple of years. We’ve seen matches like Stipe Miocic vs. Daniel Cormier, TJ Dillashaw vs. Henry Cejudo, and Amanda Nunes vs. Cris Cyborg. While they’re fun, for the most part, they also tend to hold up each division’s respective title picture.
However, it’s hard not to become excited when thinking about the possibility of a super fight between Khabib – the UFC Lightweight champ – and UFC Welterweight kingpin Kamaru Usman. Sure, it’d be hard to call Khabib a deserving challenger at 170lbs, but if it were his final fight as he attempted to go 30-0, it’d still be a must-watch.
Usman would actually represent perhaps the toughest challenge for The Eagle to go up against, period. A hulking 170lber with ridiculous physical skill, Usman is one of the best wrestlers that the UFC has ever seen at Welterweight.
And far from being one-dimensional, The Nigerian Nightmare is now highly dangerous with his strikes, too – as Colby Covington found out at UFC 245 in 2019.
Usman himself has played down any possibility of a fight between himself and Khabib, stating that there’s too much mutual respect between the two for it to happen. However, they’ve never been training partners, and if the UFC were to offer them millions to do it? Usman’s mind may just be changed.
And if Khabib were to beat The Nigerian Nightmare, not only would he become a two-division champion – still a rare accomplishment in the UFC – but it’d also be hard to dispute his spot as the greatest fighter of all time.
#5 Khabib vs. Jorge Masvidal

If the UFC were unable – or unwilling – to put together a super fight between Khabib and Usman, another potential opponent for the Dagestani could be lurking in the Welterweight division. This fighter has also fought on plenty of occasions at 155lbs – and could be persuaded to either move back down or agree on a catchweight for this clash. His name? Jorge Masvidal.
Gamebred might’ve come up short in his quest to win the UFC Welterweight crown when he was defeated by Usman in July. However, he’s still one of the UFC’s biggest stars. The event that the Usman/Masvidal fight headlined – UFC 251 – reportedly drew 1.3 million pay-per-view buys.
And given Usman had never reached those kind of numbers before, it’s safe to say that Masvidal is a major drawing card.
That alone would make him a viable opponent for Khabib, with a major pay-per-view buy-rate almost guaranteed if the two men faced off. But this fight actually makes sense from more than just a financial perspective. It’d also be a huge test for both fighters in terms of their in-cage skills.
Masvidal has defeated top wrestlers before – his KO of Ben Askren remains unforgettable. But he was thoroughly outgrappled by Usman. Could he close that hole in his game in order to take out Khabib?
And on the flip-side, Khabib has never really faced an opponent with the mix of technical striking and street smarts that Masvidal could bring. Add in the fact that both men are excellent at talking trash and building a fight – particularly Masvidal – and you could have the recipe for a feud to rival Khabib vs. McGregor.
If the UFC wants to give Khabib an opponent that’d drive up interest both financially and from a sporting perspective, without impacting any title picture, then Masvidal would work perfectly.